


My Brother's Best Friend

by scerek



Series: My Best Friend's Brother [6]
Category: Teen Wolf (TV)
Genre: Alternate Universe - High School, Alternate Universe - Human, Derek Hale & Stiles Stilinski are Siblings, Derek Hale Has a Big Dick, Double Penetration, Face-Fucking, First Time, Freshman Scott McCall, Jock Derek Hale, Jock Jordan Parrish, Loss of Virginity, M/M, Rimming, Senior Derek Hale, Senior Jordan Parrish, Slut Scott McCall, Spitroasting, Teen Derek Hale, Teen Jordan Parrish, Threesome - M/M/M, Virgin Scott McCall
Language: English
Status: Completed
Published: 2019-12-17
Updated: 2019-12-17
Packaged: 2021-02-26 07:54:47
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,728
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21830053
Author URL: https://archiveofourown.org/users/scerek/pseuds/scerek
Summary: He had been waiting for this moment all week and now all of his patience was paying off. Derek Hale, the popular senior basketball jock, was going to take geeky little freshman Scott McCall's virginity.(Or, Scott gets a special surprise for his first time.)
Relationships: Derek Hale/Scott McCall, Derek Hale/Scott McCall/Jordan Parrish, Scott McCall/Jordan Parrish
Series: My Best Friend's Brother [6]
Series URL: https://archiveofourown.org/series/945066
Comments: 17
Kudos: 168





	My Brother's Best Friend

**Author's Note:**

> **Minor Characters:** Stiles Stilinski, Talia Hale, Sheriff Stilinski  
>  **Background Relationships:** Talia Hale/Sheriff Stilinski (mentioned)
> 
> It's finally done! The epic conclusion to this series! I have to shed a tear. Thank you to all the loyal readers who kept coming to me to finish this series. I'm glad I was finally motivated to do just that.
> 
> Enjoy!

Derek Hale and his mother had been living with the Stilinskis since his sophomore year of high school. Noah was a nice guy, which was cool, Derek guessed. Better than being a deadbeat like his dad who had never bothered to contact any of his family members since he left unexpectedly. He didn't really care though. He just wanted stability for his mom, and if Sheriff Stilinski was the man to do it, Derek was fine with it.

With Sheriff Stilinski, however, came his son, Stiles. Stile was an annoying little shit who never knew when to shut up, never knew when to keep his nose out of other people's business, and he never ceased to be a thorn in Derek's side. Don't get Derek wrong though. He did care about the kid as if he were his own brother, but sometimes, he'd still long for that period in between when Laura went off to college and before his mom met the sheriff.

The best thing about Stiles, however, Derek would later learn, was the company he kept: Scott.

Scott McCall was a dork. He was nothing more than Stiles' geeky little hanger-on. The kids at school either ignored him or used him for target practice during lacrosse. Why the kid ever thought he had a chance at being an athlete was beyond Derek since the kid had the lungs of an 80-year-old man and had as much grace as Stiles on a freshly-mopped floor.

And most of all, the little freshman geek just seemed super awkward. He was always nice and polite, but was always shy and quiet around big crowds. He was an asthmatic lamb in a lion's den. But around Stiles, he was more playful and hyper. If there was ever a trait of Stiles that Derek could admire, it was that he could bring out the best in people, namely Scott.

Derek had shrugged his shoulders, seemingly uninterested, when his mother told him that Scott would be staying with them for an entire week while his parents sorted out their divorce. Scott's dad was kind of an prick, a trait too often seen in the fathers of Beacon Hills. Except maybe Noah. Noah was a decent guy in a sea of insufferable pricks. Derek felt sorry for Scott, because for how annoying the kid was, Derek could sympathize with someone who had a shit dad.

Everything changed, however, when Talia took Stiles to his dental appointment one morning. The sheriff was already at work, so it was just him and Scott. This was around the time when Derek would go out for his morning jog, so he left Scott a warning that the house better not be on fire by the time he got back or else he'd pound the little shit into the ground.

He had already walked out of the house and was almost halfway down the block when he took out his iPhone to listen to music, but realized he had forgotten his headphones so he doubled back. When Derek climbed up the stairs, he noticed his door was open and he definitely did not leave it open when he left, which meant that Scott was in his room without his permission.

Derek had seen red when he came to this conclusion and he marched into his room to a sight he did not expect to see. He guessed that Scott was playing around on his Gibson Les Paul or surfing his computer for porn or anime or whatever geeks like him were into. What he didn't expect to see was Scott lying on his bed, his hand down his pants, sniffing Derek's underwear.

Derek had stopped, mouth open in shock. The kid had literally been moaning like a whore while he took deep, long whiffs of his boxers. He always knew the kid was a freak, but this had been another level.

Derek settled on scaring the kid, angrily demanding what the dork freshman had been doing with his face in Derek's Calvins. The kid practically leapt into the air before Derek was chasing him out of his room. He knew he should've told Talia and Noah about what happened, but he opted not to. He wasn't sure why at the time, but when he had time to think about the incident, he kind of got a little of bit of an ego boost knowing that the Stiles' loser best friend had been perving on him.

He figured he might as well let Scott sweat it out. He could tell at dinner that the kid was on edge the entire time, always sending worrying glances Derek's way as if Derek was going to bring up that Scott was smelling his briefs while spanking it. It would've been great dinner time conversation, but Derek just happily gulped down his shrimp fried rice and let the little geek wet himself.

And that was when the fun had really begun. Since that incident with the boxers, Scott had definitely peaked Derek's interest. He always knew Scott as Stiles' shadow who had no other friends but Stiles, which was pretty sad on its own. But what Derek never knew about Scott was that the kid was a huge fucking slut and what Derek saw when he caught Scott staring at him in the bathroom while he shaved was an opportunity.

He had pushed the kid up against the bathroom door and kissed the life out of him. The dork had probably never kissed anyone before that moment. Derek was more than happy to be the kid's first for, very likely, everything. And he meant _everything_.

The kid had been a natural. Somehow, he knew exactly what to do when he got Derek's monster cock in his mouth. Derek was a prideful dude. He knew what he had swinging between his legs. All the guys in the locker room would stare at him. Everything about Derek could make any man insecure. From his broad shoulders to his hard abs to his thick thighs and even his ass, which was round and full. Derek's huge cock was just salt in the wound. He could tell from the way Scott would look up at him, lips stretched out from Derek's thick meat with spit trailing down his crooked chin, that he worshipped Derek and that was the real ego boost.

That twinkle in the kid's watery eyes as he looked at Derek like he was in love. It was easy to be in love with Derek Hale when one had all nine-and-a-half inches of Derek's pride and joy down their throat. Not to mention, a heaping of that creamy Hale sweetener that Scott gulped down with unbridled glee. It didn't take much for the kid to be gone and pretty much follow Derek around like a lost puppy that humps your leg at any given chance.

Several more encounters had occurred. One in the downstairs shower at the risk of being caught by Sheriff Stilinski, which only made it more exciting. And another time in the school parking lot at the risk of being caught by pretty much anyone. Except that time, they actually were caught. By Derek's best friend Jordan Parrish. After that, Derek had found himself in the middle (or technically speaking, Scott found himself in the middle) of a hot three-way of cocks getting sucked and asses getting eaten.

From the moment Scott's virgin hole touched his tongue, he knew that his cock was going in there. That he would be the one to stretch out that hole and ruin him for any future lovers. Because once Derek Hale fucked you, you were gone. You would have ascended. Nothing else will ever compare. And the best thing about Scott was that he was eager to please. He was all too happy to be the perfect slut that Derek always wanted. These high school girls were nice enough, but there was something about the enthusiasm and the charisma that the normally timid Scott had that put him above the rest. That curiosity and willingness to let Derek teach him everything he needed to know.

Scott seemed all too happy to do whatever it took to bring Derek to completion. Like it was his life goal to have Derek cum inside him, any which way he could, and that was exactly what Derek wanted in a sex partner.

And the timing was perfect. It was the last night that Scott would be staying at their house. Derek didn't know how long he had until he and Scott could be together again. And as the stars above would have it, his mom and the sheriff wouldn't be home until way late into the night. He'd had a date that night, but Jennifer bailed and he was honestly thankful because she was kind of a plain Jane and a bit uptight, and he was horny and needed to get off. Cue a movie night with his dorky stepbrother and his even dorkier slut of a best friend and you have a recipe for a good time.

Stiles was none the wiser when he goaded Scott into going down on his shaft while Stiles was barely three feet away from them, eyes glued to the screen as he watched some cheesy alien invasion flick. Even when Derek came, somehow Stiles never even figured out what was going on. 

At one point during the film, Stiles had left to go to the bathroom to drop a deuce, which left Derek to have his way with Scott. The way the little freshman geek blushed as Derek folded his legs and dove his head into his ass until he was a blubbering mess, it made Derek want to cum a second time. All while knowing that Stiles could trudge down the stairs at any given moment and see what had been going on during his absence.

The risk of getting caught had always excited Derek. One might even call him a bit of an exhibitionist with how often he'd like to strut around the locker rooms, peacocking and putting the guys on the basketball team to shame. But the idea of having sex in public was exhilarating. Once he popped Scott's cherry, he'd have to bring the kid and fuck him out into the open where anyone could catch them. Maybe even have some random stranger come in and fuck Scott with Derek. That'd be pretty hot.

But for tonight, he had one goal. They had been anticipating it all week and now it was finally time for the big finale. Derek Hale, the hot, grouchy basketball jock and de facto king of Beacon Hills High, was going to take geeky freshman loser Scott McCall's virginity.

It was the usual thing they did. They'd go to their bedrooms. Scott would be in Stiles' room, waiting. Stiles would be out like light from the inevitable sugar crash he got when he ate all that candy he shouldn't have been having. Derek would be in his room, waiting patiently. He already had everything he needed for the big event. He even had a special surprise for Scott once he came down the hall. And he would be coming down the hall, because all week Scott had been sneaking into his room to suck him off. Because Scott needed some warm Hale milk before going to bed. There was no way he was going to miss this opportunity.

Derek was on his bed in nothing but a pair of tight, black boxer-briefs, the same pair that Scott had shoved into his face when all of this craziness started. It would be the most poetic way to end this week. And if he was being honest, he finally understood why the little perv was sniffing his underwear. Derek looked fucking incredible.

A tentative knock came at the door and Derek knew it was showtime.

"Come in," Derek answered before the door opened and Scott shuffled in, blushing and nervous. It was honestly adorable. The kid really did look like a puppy in human form. Derek was going to enjoy ruining that virgin ass.

He was wearing a Captain America t-shirt that was a couple of sizes too big for his small frame along with a pair of flannel pajama shorts that were also a little too big on him. He looked innocent but Derek could tell that his chest was beating and the balls of his feet were bouncing in anticipation. He was staring at Derek like he was a work of art and he couldn't blame him for it. The kid had been idolizing him since before they were even fooling around with each other. Seeing Derek lying in bed as he was must've been a sight to behold. One hand lazily thrown on his solid abs, the other behind his head, showing offf his huge bicep, his thick, hairy legs splayed out with his bulge jutting out from his tight boxers. He was surprised Scott hadn't cum in his pants on the spot.

"Get over here," Derek said. It was not a suggestion.

Scott pulled on the hem of shirt and had been in the process of getting it over his head when Derek's commanding voice filled the quiet room in a stern tone. "I didn't say to take off your clothes," he said. "I said _get over here._ "

Little Scott gulped and staggered over ungracefully as if he was tripping over his pant leg. He got to the bed and sat down next to Derek. He was breathing real hard. Derek thought he might have an asthma attack. Scott didn't even try to conceal the way his eyes trailed over Derek's god-like body, his pupils blown out in lust.

Derek sat up and looked Scott up and down. "You ready for this?"

Derek knew Scott wasn't going to say no. Scott was too far gone under Derek's spell to say no. He wanted this even more than Derek did. He didn't say anything. He just nodded his head with an adorably naive look on his face as Derek scooted back to make room for Scott who awkwardly lied back against the bed, stiff as a board.

And speaking of stiff: Scott's cock was already rock solid and tenting his pajama bottoms. Even though he was a dweeb, Scott had a pretty nice dick. Derek could vouch for that. And he had an even better ass. Derek could definitely vouch for that. That tight ass was something Derek had had a craving for since he first ate it out, something he would never admit out loud.

To calm Scott's nerves, he moved closer to the young freshman, intimately close. He ghosted a hand over his clothed body before reaching the strip of skin between the hem of the shirts and the top of the pajamas before his rough fingers were touching with Scott's skin. The burning hot contact made Scott suck in a breath, toes curling. Derek wondered if Scott was about to cum right there in his pants.

Gradually, he moved his fingers upward, the pads of his fingers just barely brushing against the kid's still-defining abs. Scott had been looking up at him with trusting eyes. He seemed to go slack at the simple contact, eyelids fluttering beautifully as Derek went for broke and full on shoved his entire hand up Scott's shirt and felt around the entire chest. The kid had a nice body, even though he was almost hilariously unathletic as his garrulous best buddy. His muscles went tense as the little freshman gasped at the way Derek's thumb rubbed circles over his sensitive nipples.

"Please," he begged. And that was it.

Derek crashed their lips together, almost growling into the geek's mouth as he ravished him. He told Scott not to get undressed because he wanted the pleasure of stripping the loser himself. He wanted to hear the whines and moans as Derek gradually removed his sleep clothes.

All week the kid had been servicing him and if Derek wanted, Scott would happily continue worshipping him without even getting off himself. But tonight, Derek was going to make it about Scott's needs. Tonight, Scott was going to finally get his reward for being an obedient fucktoy.

Derek slipped Scott's pajama bottoms off his feet and tossed the aside. Scott was naked and splayed out like a five-course meal for Derek to feast on. There were so many options for where he could start, but he opted to put his mouth on the kid's sensitive nipples, making him whine and almost thrash about from the sensation. His mouth trailed downwards over the kid's still-defining abs, taking extra special attention to the kid's belly button. It seemed almost every trace of skin on Scott was sensitive to Derek's touch.

The boy's cock was rock hard and leaking over his stomach where Derek could taste the salt of his precum on his lips as he got lower and lower. He purposely kept himself from touching Scott's cock, torturing the boy. He was aching for release, but Derek wanted him to last longer because they had a long night ahead of them.

His kisses eventually led down Scott's thigh and down his legs before he pressed a few pecks to the hollow of his foot and then let go. Scott was looking up at him like he had all the answers to the world. Like Derek was a new god for him to worship.

Derek grabbed Scott's sides and effortlessly flipped him over, canting his hips up so that the boy's sweet hole was hiked up and exposed to him. He licked his lips hungrily and pressed a kiss to the entrance, making the kid groan with want. He could have done this all night if he wanted to. The kid had the best tasting ass he'd ever laid his mouth on.

Suddenly, his phone vibrated, interrupting their moment. Scott was panting, looking very touch-sensitive, as Derek answered his text. Much to Scott's disappointment, Derek left the room, but not before ordering Scott to stay in his exact position until he got back. So Scott just laid there with his ass out, feeling the cold breeze against his spit-slick hole as he impatiently waited for Derek to return.

Thankfully, he hadn't had to wait long before he heard the door opening and closing. And soon he felt a strong pair of hands massaging over his ass before a thumb started rubbing at his rim. Scott bit his lip to stifle the moan in his throat, but he couldn't help but whimper when he felt his ass being ravished by a hot tongue.

"How does that feel, baby?" he heard Derek whisper into his ear.

He was so fucked out, that it took him a minute for him to realize that Derek couldn't be eating his ass out and also whispering into his ear at the same time. It finally registered to him that someone else was here with him and Derek. He bolted up, righting himself on his hands as he looked over his shoulder to see none other than Jordan Parrish with his face buried in his ass.

Derek placed a hand over Scott's face, rubbing his thumb against his cheek as Scott started sobbing from Jordan's tongue entering him.

"It's okay," Derek cooed, "You like your surprise."

Scott whimpered at him, which was the best response he would get because Scott was incoherent at this point.

Eventually, Jordan pulled off and he and Derek switched places. Derek began licking into Scott's slick ass as Jordan slipped out of his basketball shorts, exposing his long cock. He had given himself a few tugs before the hard shaft disappeared into Scott's willing mouth.

"Fuck! His mouth feels so good," Jordan groaned as he fucked into Scott.

The little dork was making the sluttiest gagging noises with each thrust of Jordan's cock hitting the back of his throat. Derek could see the kid's eyes welling up, almost glittering as he was being used by the two hot senior basketball stars that he idolized so much.

When he satisfied that Scott's hole was slick enough he motioned for Jordan to get the lube out from his nightstand. He squeezed a generous amount onto his fingertips before pressing them against Scott's entrance. He easily slipped a finger into the tight heat, causing Scott to shudder so hard, Jordan felt it on his cock. Then he added another finger and marveled at the way Scott opened up to him so willingly.

By the time he got to three fingers, he felt that Scott was already stretched out enough and stood up to align his cock against the small entrance. His thick head pushed in and he could hear Scott give a small whine that was muffled from Jordan's dick. Derek bottomed out and sheathed himself in Scott's ass. He threw his head back as he reveled in the hot tightness that was Scott's ass. He was inside Scott. At this point forward, Scott McCall was officially no longer a virgin.

Scott, on the hand, was squealing from the sudden fullness and he balled the bed sheets into his tight fists trying to fight down the pain.

"Shh," Derek cooed as he rubbed Scott's lower back comfortingly. It seemed to have calmed him down enough because he was back to slurping on Jordan's cock while the jock continued using his face like a fleshlight.

When he was sure Scott had fully settled down, he gave an experimental thrust. Scott's pained whimpers eventually turned into pleasured moans and he was happily accepting Derek breaching him. He began to fuck Scott in the way he's been picturing since he caught him sniffing his boxers.

"Fuck," Derek hissed. Scott was tight, virgin tight. But his cock was sliding inside Scott with ease. It was a sweet contradiction. The kid was a natural dicksucker, it was only logical for him to be a natural at taking Derek's huge cock as well.

"Man, he's taking it so well," Jordan crowed as he picked up the pace. There was globs of spit trailing down Scott's crooked jaw and happy tears were streaming from his eyes. "Oh, fuck, I'm gonna cum," Jordan announced, his pace getting rougher. "I'm gonna cum."

His skin had gone pink and he let out a loud grunt before spilling into Scott's eager mouth. Finally, he pulled away. A thick rope of spit mixed with his cum was separating the two. Scott didn't have much time to catch his breath before he was crying out with every hard thrust Derek did.

He had been full on sobbing by the time Derek had him buried into the mattress. One hand was on his face, pushing him further down, while the other was on his hip as Derek pistoned into him. Jordan was off on the sides, nursing his deflated cock as he watched his best friend fuck his stepbrother's best friend.

Derek reached a stopping point, letting the little punk get some air. He was breathing heavily like he was having one of his asthma attacks and his hair was matted with sweat. Not long after, Derek was scooping him up in his arms and carrying him so that he was being sandwiched between himself and Jordan. It hadn't taken long before Jordan was back to full mast and pressing their bodies against each other. Derek had his chest against Scott's back, kissing his tiny shoulders as Jordan began ravishing the hollow of his neck. And all Scott could do was let himself be consumed by the these two gods.

"You ready?" Derek whispered, nibbling at Scott's ear.

Scott probably wasn't even sure what he was agreeing to be ready for. He just nodded his head while Jordan smirked mischievously at Derek. Derek snaked his arms under Scott's pits and easily lifted him so that Jordan could hook his legs around his waist. Both of their large cocks were positioned perfectly over his sensitive rim and even in his sex-hazed stupor, Scott should know what was going to come next.

Derek entered him first and he slipped in pretty easily. The boy's canals felt already full against Derek's length, so Jordan was going to have his work cut out for him. Still, his best friend was already lining himself up. He pushed himself in, stretching Scott to his limits and beyond. There were no words from Scott, just jumbled whimpers. Derek was unsure of it pleasure or pain or both, but the noises Scott made would get louder with each inch he took of Jordan's dick.

It got to a point where he could no longer make full sobs. Any time he made a noise, he had to swallow it with every thrust from the two senior jocks. He was incoherent, almost unintelligible. He was being split apart and from the way he happily bounced on both their cocks, he was loving every second of it.

"Fuck, he's perfect," Jordan panted, sucking a bruise into Scott's neck.

Derek let out a possessive grunt. He could tell from the way he was looking at him that Jordan was fond of Scott, which was just fine. Scott was an easy enough guy to fall for, not that Derek would know because if anyone was falling for anyone, it was Scott to Derek. That much was obvious, but that didn't mean that Derek didn't feel a little attachment to the little freshman dork. Despite the fact that he let Jordan be inside Scott at the same time as him, Derek wasn't willing to share his toys all the time.

Scott's head lolled back against Derek's shoulder like he was delirious and from his angle, Derek could see Scott's eyes had almost glazed over. He was still breathing hard but it was slower this time, like he had passed out from the over-stimulation from getting fucked by two huge slabs of teen beef at once.

Both boys slowed down their pace, allowing Scott to wake up and recollect himself. They stumbled backwards, still inside Scott until Jordan was falling backwards on Derek's bed. The angle made it easier for Derek to continue fucking into Scott while Scott straddled Jordan.

Jordan had the easiest job of the three. All he had to do was lie there and let his boy fuck himself on his cock while his best friend pummeled into the poor boy's too full ass. Derek leaned into Scott, pushing him further down until he was pinned between himself and Jordan. There was no escape for him. The only way out was for Derek and Jordan to cum inside him and he had to ride it out until they did.

"I'm close again," Jordan said suddenly. Derek couldn't help but smirk because his best friend was already about to cum twice and he hadn't even came once. He was definitely going to clown him about this later. But right now, they had a tight virgin ass to ruin for all future lovers.

Their need for release had caused their movements to become erratic. The heat from sliding against Jordan's cock was starting to get too much even for the basketball star stud himself. He wasn't entirely sure who came first between the two of them, but if he had to guess, it was Derek who was filling Scott out with Jordan cumming not long after. Scott felt so full and so fucked out, that the only thing he could manage to do was scream aloud while he made a sticky mess between himself and Jordan.

They lied in place, not wanting to detach from each other just yet. Instead, Scott planted a sloppy kiss to Jordan's lips. He pulled away and craned his head as best as he could to give Derek a kiss too. A perfect way to end his first time.

"Holy shit," came a surprised voice.

The three of them froze in place. Scott looked like a ghost while Jordan just looked confused. They turned to see Stiles standing in the doorway with his mouth hanging open in shock.

"Wh-what are you guys doing?" he squeaked, eyes darting all over the place.

Derek furrowed his eyebrows at him. "What the fuck does it look like?" he growled, "I'm fucking your best friend!"

**Author's Note:**

> I'm well aware this kind of ends in a cliffhanger, but the series was supposed to end with Scott losing his virginity so this is where I've chosen to officially ends this. But that doesn't mean the fun will stop there. There's always potential for more extra fun stuff after this.


End file.
